


Fair Games

by MidnightRamblings



Category: Supernatural
Genre: F/M, Foreplay on a Ferris Wheel, Hand & Finger Kink, Hand Jobs, Public Hand Jobs, Resolved Sexual Tension, Sex, Sexual Content, Smut, State Fair, fun house, vengeful spirit
Language: English
Status: Completed
Published: 2016-09-06
Updated: 2016-09-06
Packaged: 2018-08-13 07:55:21
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,676
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7968583
Author URL: https://archiveofourown.org/users/MidnightRamblings/pseuds/MidnightRamblings
Summary: <blockquote class="userstuff">
              <p>When a vengeful spirit starts attacking people at the fun house you work at the Winchester's turn up to solve the case. When you survive a brush with a monster, Dean nurses you back to health and you repay him by showing all the fair can offer... and a little more.</p>
            </blockquote>





	1. The Fun House

You stood behind the tape and looked as the police scampered in and out of the fun house. You hated this job, but your father basically forced it upon you. He had worked the midways across 3 or 4 states your entire life. You had spent summers on the road going from town to town and when you were little it was fun, like an endless party where no one was watching you and you could just ride the rides and eat candy all day. Once you hit 13 though your dad put you to work, calling games or collecting ride tickets. Now, it seemed like both a safe haven and a dead end and when you found yourself failing out of college sophomore year with no discernible prospects for jobs you fell into the only thing you really knew how to do. You came home to the midway, your extended family welcoming you back with open arms, even though your dad had died several years before. For 3 years your life had been on the road, moving with the fair, setting up and taking down rides, watching happy families drift in and out while missing your own.

This particular stretch had been bad. You had gone to pick up some new rides with some other workers and it seemed like the last 3 weeks of the fair had been plagued with bad luck. On your second day a girl was attacked and stumbled out the front on the Fun House with torn clothes and scratches covering her legs, she said that something grabbed her in the mirror maze and tried to pull her into a mirror, but the security video showed nothing. Just her walking through with friends and then her coming out looking a mess. Police had come then too, but couldn’t find anything, in fact they suspected that it was all a prank since even the girl’s friends didn’t seem overly concerned. During the 2nd week a girl disappeared at the fair. According to her boyfriend she had gone into the Fun House and never come out, but you didn’t remember seeing her at all. You suspected the girl actually just ran off, the boyfriend was a bit of a skeeze anyways. Today was different though, today it would be hard to explain it away, today a girl died.

“Excuse me? Miss?” Your eyes snapped away from the Fun House doors and traveled up to meet those of the person talking to you. He was impossibly tall, towering over your 5’10” and he looked haggard and worn. “The officer said you were working the Fun House when this happened?”

You tilted your head and narrowed your eyes a bit. “Yeah. And you are….” You let the question hang in the air.

“Sorry, FBI” He flashed his badge and a smile. “Agent Smith. Over there is my partner Agent Wesson. Your name?”

You snorted back a laugh and shook your head. “Sure ya are. Why don’t you go ahead and call me Annie Oakley since we’re picking aliases out?”

Agent “Smith” paused then and looked at you, like he was trying to figure you out. “Fine. Sam Winchester and my brother Dean.”

“Okay... might want to move away from the gun names though. Do people actually buy that? Smith, Wesson, Winchester… does your fake CIA badge say Colt on it? And just for the record, is that shaggy mane of yours really up to the FBI’s dress code?”

Sam ran a hand back through his hair as he looked over his shoulder at Dean who was walking your way with a grim look on his face. “Listen. We are here because what’s happening in your Fun House is not normal. In fact, the world is full of monsters and the thing that’s doing it is going to keep doing it until we stop it. Do you understand?”

Dean slid up next to his brother and looked back and forth between to two of you. “Little early for the monster talk isn’t it, Sammy. Might scare the little lady.” Dean tossed a wink your way and smiled.

You cocked your head to the side and raised an eyebrow at Dean. He was smaller than Sam and more slightly built, but you could tell that he was solid muscle under his suit. His green eyes stared back at you and you let your gaze float across his face, noticing the trail of freckles that disappeared into his shirt collar. With a small sigh you smirked and looked back at the boys, “Wow. You guys are quite the pair. So far you’ve trespassed into a crime scene, lied to me about who you are and now your, what? Treating me like some little girl? Well, thank goodness you big strong men are here to protect me. Whatever would I do without you?”

Dean fixed you with a hard stare. “Listen lady. This nonsense isn’t helping anyone. Without us you’d probably die, okay? Sam’s right, whatever is in there isn’t going to stop and even if you survive the next few days then this thing will probably get someone else at the next stop. So cut the shit and either help us out or get out of the way.”

Sam stared open mouthed at his brother, “Jesus Dean, don’t you think…” He trailed off when both you and his brother cut him a nasty look.

“Cut the shit? Yeah, sure. I’ll cut the shit, but first can I just say ‘pot, meet fucking kettle’. Do I need to remind you that you assholes are the ones who came to me tossing lies at me left and right like I’m an idiot? I’ll repeat, do people buy your fucking act? At this point you need me a hell of a lot more then I need you, so I suggest _you_ cut the shit and try treating me with a little fucking respect.” You squared off in front the two men, hands clenched at your sides, trying to control your anger. You were so sick of being treated like something simple and breakable. You certainly weren’t going to take it from these two.

Dean broke first, a wide smile spreading across his face, lighting up his green eyes. “I like her Sammy.” He said clapping his taller brother on the shoulder. “I like her a lot. I have a feeling this is going to be a fun one.”

Sam ducked his head and his hair fell across his face. He looked back up at Dean before turning to you, a slow smile creeping in, ”Yeah, okay. Just… can we do some research and try not to kill each other?” he looked back and forth between you and Dean again “Annie? Can you help us out here please?”

You broke your gaze from Dean’s face and looked at Sam “You know my name's not Annie, right?” Sam laughed and shook his head and just like that the tension broke and you followed the two brothers to a table near one of the food stands. The conversation flowed as they filled you in about the world of monsters and what they thought might be doing this (vengeful spirit apparently) and you gave them the inside scoop on the fair and the rides, telling them about the place you had picked the ride up from and making plans to reconnect after they went to check it out. You stood at the end of the midway watching them go, wondering what they would find out.


	2. A Maze of Mirrors

**Summary for the Chapter:**

> You join the Winchesters on the hunt and come face to face with your first monster.

The next few days seemed to crawl by as you watched as Sam and Dean tracked down the original owners of the Fun House and through some digging discovered that a boy had died there almost 5 years ago. He had been attacked by this girl that he had liked. She and her friends had lured him into the Fun House, pretending that she wanted to date him. It was supposed to be a joke, but it wasn’t funny.  When they walked into the mirror maze the girl’s friends had emerged and surrounded him, their numbers multiplied by their reflections. Taunting him and calling him names. When he tried to run he tripped and fell into one of the girls and when she pushed him off he slammed his head into the corner of a mirror. He died shortly after.

Sam told you the whole story while you were sitting at the same picnic table across from the midway, Dean adding in details around mouthfuls of fried dough and kettle corn.

“So what do you do now?” you asked looking between Dean and Sam.

Sam dragged his hand through his hair, a move that you recognized as one he made when he was unsure of something. “We are going to need your help. It’s dangerous though.”

“Dangerous how?” You squinted at Sam and waited for a response.

“You know the Fun House better than we do. He was cremated so that means that something has to be tying him to it. Is there anywhere you can think of in there where something could have gotten stuck or overlooked? His mother said he was missing the cross that he always wore, she assumed that it was lost, but if it got caught in something as he fell it could be what’s tying him to this place.” Sam and Dean looked at you with matching looks on their faces. They were trying not to put pressure on you, but you could tell this was important. And to be honest, it sounded more exciting then dangerous.

“Yeah, of course.” You closed your eyes in thought and did a mental walk through of the fun house, thinking closely about the mirror maze. “So he fell in the maze right? Those mirrors are on hinges, so that you can turn and reposition them each day, so people can’t learn the pattern easily. When he fell it could have slipped into the track. You’d think someone along the way would have found it, but maybe not. I’d start there.”

“Great!” Dean said, balling up his paper towel and standing up. “Let’s do this.”

By the time you had gotten everything together for the hunt it was dusk, the sun slipping behind the rides and the free concert starting up in the distance, music drifting through the air. You, Sam and Dean slipped under the police tape and into the maintenance door of the fun house, turning on flash lights as you walked silently through the halls.

“Over here” you said quietly, pointing to the mirror maze. “You need to pull the pin in order to spin the mirror, you should be able to turn it and check the tracks.” You showed the boys how to do it on the closest mirror, waiting for them to both nod before moving off to the next one. There were 20 mirrors throughout the large room, assuming you were right and this is where the necklace was it shouldn’t take too long to find it.

You were on your 6th mirror when your flashlight caught a glint of gold in the track. You wedged your fingers along the edge, dragging the chain towards you until you could slip your finger into the loop. “I got it!” you whispered loudly “It’s stuck though.”

As the words left your mouth you were surprised to see a puff of air in front of your face and you stared at it a second, not quite processing what was happening. You breathed out again, watching the soft cloud drift away from your face, your body slowly chilling as the adrenaline of finding the necklace began to leave your body.

“Dean…” you called and began to turn to look for him or Sam, but instead of one the boys you found your eyes being drawn to a different face. Young and pale, staring out from the mirror across from you. You found yourself holding your breath, just looking at him as he looked back at you. He couldn’t have been more then 15, a dark trickle of blood framing the left side of his face. You glanced to the side, hoping to see Dean or Sam, but all you saw was your reflection and his, multiplied over and over around the room.

It felt like you sat there forever, but in reality only a few moments passed, and then, he moved. His fingers curved over the edge of the mirror and his eyes closed and he rolled his neck, as if to loosen it up, before pulling his body through. Crouched across from you he held your gaze and you could feel the hate roll off of him. Instinctively your body went into a defensive stance coming up to a crouch of your own across from him, your fingers curling around the necklace, tugging it free with a quick yank.

You could feel the tension snap as he lept forward with a shriek, diving for your ankles. You moved to the side as fast as you could, but he grabbed your right leg and yanked you down hard. You’re left foot kicking out into him. Your own yell echoing his.

“I’m not her!” you screamed at him, but it fell on deaf ears.

“Annie!” you heard Dean yell as he and Sam crashed into your corridor, knocking the other mirrors away as they tried to find the real you, the real spirit.

“Sam! Necklace!” You shouted, rolling your body towards the closer brother, flinging your hand out, necklace dangling from your fingers. Sam’s hand wrapped around the chain just as the spirit yanked you back down, climbing up your body, hands pulling on knees and hips, fingers digging into your flesh as he reached for your face. Hands framed your face and suddenly your entire world was the boy, this poor, dead child who shouldn’t have died. You heaved a sigh and whispered “I’m so sorry” and then the world went black.


	3. The Ferris Wheel

**Summary for the Chapter:**

> After Dean patches you up, you repay him by showing all the fair has to offer.   
> Finally, all the smut.

A few hours later you were patched up and Dean was filling you in on what you had missed after the spirit had slammed your head into the mirror. Sam had lit up the necklace just after the first impact, probably saving your life, Dean had carried you out and made sure you were alright. Then it was over. It was that quick, that simple. Sam had headed back to the motel to clean up and Dean had stayed with you. As he told the story Dean stared at you like you might break, waiting for you to crumble.

“Stop staring at me like that” you said pushing his hands away from your forehead where he was holding a damp washcloth. “I’m fine you know.”

“Sure you are Annie.” Dean said, looking away from you and over the fairgrounds. “You know, I’ve never been to a fair, not really.”

“Never? Like ever?” You looked at him as he shook his head. “Well, we fix that tonight. Rides are open for another hour or so. Live music will be blaring until the place shuts down at midnight. What do you want to do first?”

Dean looked at you and a sly smile played across his lips. “You pick. Show me your favorites.”

You spent the next hour dragging Dean from ride to ride, using your influence to get free games along the midway, grabbing bites to eat from your favorite stands. Somewhere along the way you found yourself grasping Dean’s hand, yours fitting inside his easily, a comfortable feeling washing over you both. Experiencing the fair with Dean was fun, seeing it in a newbies eyes, but along the way you also started to like the way his hand felt in yours, the way he led you through the crowds with his hand on your lower back, the way he gripped onto you on the roller coaster, his laughter mixing with yours as you prowled the midway. Eventually, you found yourselves at the base of Ferris Wheel staring up at the top and beyond that the stars.

“Wanna go for a ride?” you winked at Dean and nudged him with your hip.

“What kind of ride are you thinking?” Dean said in a low voice, a hint of a smile teasing the edges of his mouth.

You stepped closer to Dean and ran your hands down the front of his shirt, lightly pulling at the buttons. Your fingers caught at the waistband of his jeans and you pulled him sharply, his hips landing just above yours. You tilted your head up to his and moving your hand to his cheek pressed your lips to his for a light kiss. “How about we try the Ferris Wheel first and if it seems like you can handle something a little more… active… then I’ll show you what kind of ride I really like.”

Stepping into line Dean pulled you close so that his arms were around your waist, your back pressed against his chest his face resting gently on the back of your head. You heard him growl deep when you rolled your hips back into him a bit, teasing at the front of his pants with your ass, rubbing against him gently.

Soon enough it was your turn to climb into a car, and as it swung forward Dean gripped your hand tight, his eyes growing wide as you slowly lifted off the ground. You laughed lightly and squeezed Dean’s hand, “Afraid of heights?”

Dean’s eyes slipped closed and you could see him struggling to even out his breath. “Holy shit, Dean, are you afraid of heights?”

Dean’s eyes opened and he cut his glance your way, “A little bit…”

Your head fell to Dean’s shoulder as you let out a laugh. “Why didn’t you tell me? This is the slowest, highest ride here. Can you relax, do you think?”

Dean closed his eyes again, his head tilting back to lean on the seat. “Maybe. Maybe if I don’t open my eyes. We can just sit here and I can pretend I’m on the ground.”

You felt awful. It's not like you could have known that he was afraid of heights, but you wished he had told you, you never would have made him get on. For a little while you just sat, hands pressed together, your knees brushing against each other as Dean’s muscles tensed and relaxed every time the car swung. Eventually you started telling Dean what you were seeing... kids playing darts on the midway, a couple kissing by the tilt-a-whirl, a group of young boys trying to outdo each other at the strong man challenge, an elderly couple dancing to the band. It was a cover band, playing classic rock and you could hear the chorus of REO Speedwagon’s **_“I’m Gunna Keep on Loving You”_** ghosting by on the wind. You leaned your head back next to Dean’s and with your head next to his you could hear him singing low, the words barely a whisper.

You slid your hand from Dean’s and put your hand on his thigh, feeling the muscles begin to go lax, you ran your hand down towards his knee and then dragged it back up again, almost to the hip. You heard Dean suck in a tight breath. You looked at Dean’s face, his eyes hooded, lips slightly parted and you turned your body towards his, the car swinging slightly at the movement. You slowly pressed your lips to his, one hand still on his thigh, the other pressing onto his chest, you could swear you could feel his heart beat through the shirt.

“Annie…” Dean breathed into your mouth. As his lips parted on your name, well, your new nickname, you slid your tongue in, tasting the sugar on his lips. When Dean pressed back into you the car began to swing again and Dean tensed back up, his mouth freezing under yours, hand gripping the arm rest tightly.

“Relax Dean, the car’s not going anywhere.” Your hand slid down Dean’s chest and rested on the buckle of his belt, your mouth sliding from his and over to his neck, teeth nipping at his ear as it swept by. Without looking you unhooked his belt and fingered the button open, sliding the zipper down slowly, pressing your hand against him. “Relax”

Dean groaned and you could see his adams apple bounce as he swallowed the noise down. “Don’t worry. No one can see us. We have at least 5 more cars until we start heading down again, so I’ve got some time to take your mind off your fear, maybe give a little taste of what might be coming later. I mean, if you’re still interested in going for another ride?” Your hand was cupping Dean lightly, squeezing and rubbing gently as you talked, eyes never leaving Dean’s face. As you felt him grow hard you brought your hand to your mouth, sucking your fingers in, tongue flicking out to coat your palm.

“Jesus Annie” Dean growled as you brought your hand back to his waist, sliding past his boxers and gripping him tightly, pumping up and down slowly, using the dribble of precum to further coat his shaft,  feeling him twitch in your hand. Suddenly Dean’s hand clamped down on your wrist and you stilled under his touch. His eyes were blown wide open and his breath came in short bursts. “How many more cars?” Dean gasped.

You turned your head and counted the cars beneath you. “Four.”

“Can’t come here, Annie girl. Wanna get you somewhere and get you naked and make you scream.” Dean’s head was tipped forward, his hand still wrapped around your wrist.

A laugh bubbled up from your throat, ringing out loudly and Dean turned his head to you, eyes narrowed at your outburst. “I’m sorry” you said sliding your hand out of his pants “Did you just cock block yourself?”

Dean groaned through gritted teeth as he zipped himself back up. “I prefer to think of it as prolonging the pleasure. Make no mistake sweetheart, my cock is going to be just fine.” A wicked grin emerged on his lips and his hands slipped over to you, one wrapping around the back of your neck, the other sliding between your legs, rubbing you slowly through your jeans. “Are you wet yet Annie? I can’t feel it through your jeans, but I’m willing to bet I could dip a finger into you right now and find you ready to go.”

You pressed your lips into Dean’s and rocked your hips into his hand, a small moan leaving your mouth as Dean increased the speed. As you broke away you looked out and saw that you were the next car to unload. “My trailer…” you gasped as Dean nodded quickly.

As soon as the worker unlocked your door you both hit the ground ready to move. Dean had no idea where your trailer was, so you found yourself tugging him along between tents and buildings, hands grasping at each other as you moved swiftly. Soon you were at your door, stumbling up the steps with Dean’s lips on your neck, fumbling for keys as he gripped you breasts from behind, teasing a nipple through your shirt. You head dropped forward onto the doorframe as you let out a small moan and melted back into Dean, his hips pressed tightly to your ass. After a deep breath and a massive amount of concentration you were able to get the key in the door and you stumbled into the small space.

As you moved through the room, clothes went flying. You pulled your shirt over your head as Dean undid the buttons on his, both discarded in the kitchenette. You fumbled for Dean’s belt and he tried to thumb open the buttons on your jeans. Shoes were kicked aside and you both stumbled to the bed, wriggling out of pants and collapsing together in just your underwear. Dean grabbed at your bra and finding the front clasp too hard to manage, simply ripped it in half, the tiny plastic clasp no match for his hands. He pushed you back onto the bed and kneeled up between your legs, eyes sweeping from your face down your body and back up again. “God dammit Annie, you’re beautiful”

“Jesus Dean, stop staring and get to fucking. I believe you told me that you were gunna get me naked and make me scream. I plan on holding you to that.” Your hands reached out for Dean, one gripping his wrist tightly and bringing it down to the edge of your underwear, the other wrapping around his neck and pulling him in for a deep kiss. When Dean’s hand slid inside your underwear and rubbed across your wet mound he let out a low, slow moan. “Why don’t you slip a finger in there and see if I’m ready” you teased into his ear, repeating his words back to him.

“Don’t need to” he growled, yanking your underwear roughly down your legs with one hand, sliding his boxers off with the other.

Your breath caught at the sight of him. He gripped his shaft tightly and moved between your legs, one finger rubbing across your clit and causing your back to arch up off the bed, your legs tipping open wider. Dean leaned across your body, pressing his mouth to your nipple, teasing it with his tongue and teeth. Just as you exhaled he slammed into you in one swift move, filling you up quickly before pulling back out slowly. Your breath came out in a puff and you moaned his name into the room. Dean set a punishing pace, the friction causing your muscles to tighten as you were pulled towards your climax.

Dean’s voice drifted over you, words jumbled with moans and growls as he sped up his pace. His hand slipped down and began rubbing your clit as he pushed in and out and you knew you wouldn’t hold on much longer. “Dean” you yelled out as your hands wrapped around him, fingers digging into his hips pulling him closer as you rolled your hips up into him over and over trying to match his moves.

“Oh god. Annie. Right there. Keep…keep doing that. Oh god. Feels so good. I can’t hold on. Cum for me, Annie, I want to feel you cum all over me.” His lips latched onto your neck and you could feel him sucking in as you gripped him tighter, pulling him in as far as he could go, his thumb speeding up.

You tipped over the edge just before Dean did, his name on your lips and your fingers gripping his hips and holding him steady as you contacted around him, feeling his cock tighten and grow before spilling into you, pulsing wave after wave of hot liquid into you. His body sagged and he pressed his lips to yours, slow kisses taking over. He rolled to the side and you followed him, trying to catch your breath and relax into him.

“What’s your real name?” Dean whispered, his hands smoothing your hair away from your face as he looked into your eyes.

You kissed his lips and ran your fingers across his cheek. “Where do you live Dean?”

Dean pulled back and met your eyes with a confused look. “On the road mostly, right?” Dean nodded, slightly. “Me too. I follow the fair, never in one place for more than a week or so. Tomorrow you’ll go your way and I will go mine. So I’ll be Annie for tonight, I’ll be Annie for you and tomorrow we’ll say goodbye, okay?”

Dean pressed his lips to yours almost desperately and pulled you close. You could feel him starting to twitch against your leg and you knew that there were a few more rounds for Annie and Agent Wesson left to go tonight and you’d carry the memory on the road with you when you left.

 


End file.
